Alkyl azides are widely used in many reactions. Although synthesis of such species is relatively well documented, fluorinated azides, especially with large perfluorinated or highly fluorinated groups, are sometimes tricky to make. The presence of fluorine in reacting molecules, sometimes causes significant changes in the reactivity of reacting species. In this paper we give a short overview of re-examination of currently available methods of synthesis of selected azides with highly fluorinated groups.
Peptidomimetics are molecules related to natural peptides that have an artificial unit incorporated in their structure. Such structural modifications, mimicking properties of natural amino acids, can be responsible for differently pronounced activity. Among others, amino acid derivatives with fluorinated olefinic motifies can act as building blocks in the synthesis of complex molecules with potential biological activity. Therefore, the synthetic approaches to the fluorinated olefinic moiety amino acids are of interest to organic chemists. There are different synthetic methods yielding fluorinated olefins having significant value in the synthesis of amino acid derivatives. This mini review describes the latest achievements in the synthesis of amino acids bearing mono-, di-or trifluorovinyl moiety.
Herein, we report the synthesis of analogues of amino acids with a monofluorovinyl moiety. Interestingly, we have found that cyclization of the obtained products proceeds easily in all cases. The cyclization process has not previously been observed at this reaction stage, and such fluorinated lactams derived from phenylalanine, valine, alanine have not been described before.
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